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In this work, we tackle this challenging transformation by the judicious combination of electrochemical conversion and chemical functionalization steps. In the first step, lignin\u2010derived <jats:italic>para<\/jats:italic>\u2010substituted guaiacols and syringols undergo an atom\u2010efficient, room\u2010temperature anodic oxidation using methanol both as solvent and reagent towards the formation of the corresponding cyclohexadienone derivatives, which are subsequently converted to synthetically challenging <jats:italic>ortho<\/jats:italic>\u2010methoxy substituted anilines by reaction with ethyl glycinate hydrochloride under mild conditions. The developed method was applied to crude lignin depolymerization bio\u2010oils, derived from reductive catalytic fractionation (RCF) mediated either by copper\u2010doped porous metal oxide (Cu<jats:sub>20<\/jats:sub>PMO) or Ru\/C, allowing the selective production of 4\u2010propanol\u20102\u2010methoxyaniline (<jats:bold>1Gb<\/jats:bold>) and 4\u2010propyl\u20102\u2010methoxyaniline (<jats:bold>2Gb<\/jats:bold>), respectively, from pine lignocellulose. Finally, the application of <jats:bold>2Gb<\/jats:bold> was further studied in the synthesis of carbazole <jats:bold>2Gc<\/jats:bold>, a lignin\u2010derived analogue of biologically active alkaloid murrayafoline A.<\/jats:p>","DOI":"10.1002\/cssc.202301374","type":"journal-article","created":{"date-parts":[[2023,11,21]],"date-time":"2023-11-21T22:27:47Z","timestamp":1700605667000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Aniline Derivatives from Lignin under Mild Conditions Enabled by Electrochemistry"],"prefix":"10.1002","volume":"17","author":[{"given":"Antonio A.","family":"Castillo\u2010Garcia","sequence":"first","affiliation":[{"name":"Institute of Chemistry University of Graz  Heinchstrasse 28 A-8010 Graz Austria"},{"name":"Stratingh Institute for Chemistry University of Groningen  Nijenborgh 4 9747 AG Groningen, Groningen The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christian Oliver","family":"Kappe","sequence":"additional","affiliation":[{"name":"Institute of Chemistry University of Graz  Heinchstrasse 28 A-8010 Graz Austria"},{"name":"Center for Continuous Flow Synthesis and Processing (CCFLOW) Research Center Pharmaceutical Engineering GmbH (RCPE)  Inffeldgasse 13 A-8010 Graz Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Cantillo","sequence":"additional","affiliation":[{"name":"Institute of Chemistry University of Graz  Heinchstrasse 28 A-8010 Graz Austria"},{"name":"Center for Continuous Flow Synthesis and Processing (CCFLOW) Research Center Pharmaceutical Engineering GmbH (RCPE)  Inffeldgasse 13 A-8010 Graz Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8046-4248","authenticated-orcid":false,"given":"Katalin","family":"Barta","sequence":"additional","affiliation":[{"name":"Institute of Chemistry University of Graz  Heinchstrasse 28 A-8010 Graz Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,12,20]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","volume-title":"Amines, Synthesis, Properties and Applications","author":"Lawrence S. 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